Chez Henri on Shepard Street closed more than 12 years ago, but the restaurant’s beloved Cubano sandwich — and the hunger for it — never disappeared. Over the years, Paul O’Connell, Chez Henri’s former owner and chef, has held several Cubano pop-ups at Mariposa Bakery, Noir, and the Warehouse XI in Union Square. This Wednesday, O’Connell’s legendary spin on the double pork handheld will make an apt pop-up appearance at Gustazo, the James Beard-cited Cuban eatery in Porter Square.
Over nearly 20 years, Chez Henri’s crisp, perfectly pressed sando became an art form with a ravenous cult following. A great Cubano is the perfect sandwich: juicy pork, lean ham, Swiss cheese, pickles, and mustard pressed on pan Cubano (Cuban bread), a French baguette, or any other airy, panini-friendly bread. That combo of pickles, mustard, and pork makes for a tangy, pucker-inducing yum — and a bit of a pleasantly gooey mess.
The Cubano pop-up concept at Gustazo, incubated by area restaurant publicist Christopher Haynes, will kick off a weekly Wednesday offering from chef and owner Patricia Estorino, who will feature her spin on the Cuban sando. Estorino will prepare her slow simmered pork as a combo of butt (meaty) and belly (a fattier cut that she says gives the blend its juice and flavor) and use Iggy’s or house-made bread.
But this week will feature O’Connell’s well-loved classic. “It’s Paul’s night,” said Estorino, who confessed to being a fan of the Chez Henri Cubano when she first came to the area.
O’Connell makes his Cubano more akin to the traditional style, with sliced slabs of tender pork, and topped with chipotle aioli. His bread of choice: Piantedosi’s soft French bread from the long-lived bakery (over 100 years) in Malden (O’Connell grew up in neighboring Melrose). O’Connell calls the bread choice — “soft” French bread from an Italian bakery — his “poorly kept dirty secret.” One of his longtime bartenders used to say about the more traditional, hard-crusted French baguette, “I hate it when they give you bread like that. They should give you a Band-Aid for when you cut your mouth eating it.”
The Cubano, as both chefs pointed out in our conversations, is an American invention that originated in the late 1800s in Ybor City, a section of Tampa. “We don’t really eat Cubano sandwiches in Cuba,” Estorino said, “I never thought to put one on the menu” — until now. In Ybor, the medley of salty dill, fatty juice, and double jamon was a working-class staple, the equivalent of a staff meal, that didn’t catch fire until the 1950s in Miami, when the mustard and pickles became more of a must than a maybe, and the hot-pressed savories were sold out of mom-and-pop bodegas. To mainstream America, the Cubano — cheap and an easy grab on the go — was Desi Arnaz haute cuisine.
Estorino, a two-time James Beard nominee, knows Cuban food intimately: She grew up in Havana and immigrated here in 2000, when her husband studied at the Longy School of Music. A professional dancer in Cuba, Estorino struggled to find similar opportunities here — the only option was the Boston Ballet or New York City. Plan B stemmed from the couple’s desire for home-style food, and so they opened a small cafe in Belmont, shifting to a bigger location in Waltham in 2013, and opening the Porter Square restaurant in 2019. The Waltham shop later moved from the Main Street location to its current spot, up the hill on Moody Street, just as the pandemic lockdown came — not a great time for the restaurant industry.
Over the past two decades, Estorino has quietly and steadily built a reputation and local following based on quality, passion, and service. In the past, we’ve extolled here the virtues of Gustazo’s crab tacos (plantain tortillas), roasted chicken, grilled octopus (pulpo), and silky, rich guac with plantain chips — which will certainly accompany the Cubanos.
O’Connell, who recently underwent two knee replacements, is a classic, salty Boston food insider. He went to Johnson & Wales University and ran Providence in Brookline besides Chez Henri (located in the space that now houses Moëca). He worked at the Parker House and beside Todd English as he launched Olive’s in Charlestown. More recently, O’Connell served up comfort nibbles with Lydia Shire (Bar Enzo) and Barbara Lynch for a family-and-friends gathering after Summer Shack founder Jasper White’s passing.
If you miss out on the pop-up Wednesday, you can always circle back the following week for Estorino’s creation. O’Connell said his version will return to Mariposa Bakery in Central Square, owned and run by O’Connell’s girlfriend, Suzanne Mermelstein.
Of his Cubano’s staying power, O’Connell said, “That sandwich just took on a life of its own.”


